WO2005055722A1 - Compositions agrochimiques - Google Patents

Compositions agrochimiques Download PDF

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Publication number
WO2005055722A1
WO2005055722A1 PCT/GB2004/005002 GB2004005002W WO2005055722A1 WO 2005055722 A1 WO2005055722 A1 WO 2005055722A1 GB 2004005002 W GB2004005002 W GB 2004005002W WO 2005055722 A1 WO2005055722 A1 WO 2005055722A1
Authority
WO
WIPO (PCT)
Prior art keywords
adjuvant
amine
agrochemical composition
agrochemical
amide
Prior art date
Application number
PCT/GB2004/005002
Other languages
English (en)
Inventor
Richard Brian Perry
John Henry Nettleton-Hammond
Patrick Joseph Mulqueen
Guy Ramsay
Original Assignee
Syngenta Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP04769042A priority Critical patent/EP1694124A1/fr
Priority to AU2004296585A priority patent/AU2004296585B2/en
Priority to CA002546780A priority patent/CA2546780A1/fr
Priority to JP2006543604A priority patent/JP2007513932A/ja
Priority to EA200601083A priority patent/EA011571B1/ru
Priority to BRPI0417405-4A priority patent/BRPI0417405A/pt
Priority to US10/578,211 priority patent/US20070082818A1/en
Priority to UAA200607534A priority patent/UA83706C2/ru
Application filed by Syngenta Limited filed Critical Syngenta Limited
Priority to NZ547047A priority patent/NZ547047A/en
Priority to AP2006003673A priority patent/AP2231A/xx
Publication of WO2005055722A1 publication Critical patent/WO2005055722A1/fr
Priority to IL175739A priority patent/IL175739A0/en
Priority to NO20062295A priority patent/NO20062295L/no
Priority to TNP2006000172A priority patent/TNSN06172A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/08—Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the present invention relates to agrochemical compositions and in particular to an aqueous composition comprising an agrochemical active ingredient and an adjuvant.
  • Agrochemical active ingredients are generally utilized in combination with an adjuvant, which is frequently a surfactant. Most commonly adjuvants are added to enhance the bioperformance of the active ingredient and many such bioperformance enhancing adjuvants are known to those skilled in the art.
  • adjuvants Most commonly adjuvants are added to enhance the bioperformance of the active ingredient and many such bioperformance enhancing adjuvants are known to those skilled in the art.
  • certain amines or amides provide effective bioperformance enhancement of the active ingredient despite having little or no surfactant properties.
  • an agrochemical composition comprising an agrochemical active ingredient and an adjuvant, preferably cyclic amines or cyclic amides having at least one tertiary amine group or tertiary nitrogen.
  • the amines or amides of the present invention are preferably an amine or amide selected from quinuclidine or a salt thereof, N-(aminopropyl) morphiline or a salt thereof, 1-(2-hydroxethyl-2-imidazolidinone) and aminoethylpiperazine or a salt thereof.
  • the amines or amides of the present invention are basic compounds and if used in their basic form may be incompatible with base-sensitive agrochemicals (such as paraquat) and, or base sensitive formulants (such as some alcohol ethoxylate surfactants); as well as being a potential hazard to human exposure. It is preferred therefore that in normal use and in particular when used with base- sensitive agrochemicals and/or formulants, the amines of the present invention are neutralized in whole or part.
  • the amines or amides of the present invention may conveniently be neutralized by the addition of acid, for example a mineral acid such as a halide acid, for example hydrochloric acid, or an organic acid such as acetic acid.
  • amines or amides of the present invention may also however be neutralized by the addition of any suitable anionic acid species, including anionic surfactants as will be described in greater detail below.
  • a salt of the amines or amides of the present invention includes the amines or amides of the present invention whether wholly or partially neutralized by an anionic species and does not necessarily imply the physical association of the amine or amide cation and the anionic species in the composition. It will generally be convenient to neutralize or partially neutralize the amines or amides of the present invention prior to incorporation in the composition of the invention.
  • agrochemical active ingredient includes without limitation herbicides, insecticides, fungicides, plant growth regulators and seed treatment agents. It is preferred that the agrochemical compositions are aqueous compositions and it is especially preferred that the agrochemical active ingredient is a water-soluble agrochemical active.
  • the aqueous agrochemical compositions may generally be applied to the target by spraying and the composition may be a concentrate which is designed to be diluted with water prior to application or may be ready for application.
  • the amines or amides of the present invention may be incorporated into the spray composition prior to application as a tank mix or may form a component of an agrochemical concentrate intended for dilution prior to use. It is a particular advantage of the salts of amines, or amides of the present invention that they are readily soluble in water and are generally compatible with water-soluble agrochemicals. Salts of amines, or amides of the present invention are thus particularly suitable to be "built-in" to a concentrate comprising a water-soluble active ingredient. Suitable agrochemical active ingredients are known to those skilled in the art and are listed in standard reference books such as the Pesticide Manual.
  • water-soluble active ingredients there may be mentioned paraquat, diquat, glyphosate, fomesafen, thiamethoxam, mesotrione, trifloxysulfuron or mixtures thereof.
  • water-soluble agrochemical is meant an agrochemical having a solubility in water of at least 1 g/l and preferably at least 4 g/l, for example at least 100 g/l. Of course many agrochemicals have a much higher solubility, for example 300 g/l or more or up to 500 or 600 g/l or more. Paraquat and diquat and mixtures thereof are particularly suitable water soluble agrochemical active ingredients.
  • aqueous compositions according to the invention contain at least 40 grams per litre of paraquat or diquat or mixtures thereof (individually or in combination referred to herein as bipyridylium salt) expressed as bipyridylium ion.
  • the compositions may contain greater than 50 grams per litre, for example greater than 100 grams per litre of bipyridylium ion.
  • Compositions containing 200 grams or more per litre may be prepared although a concentration of paraquat in excess of about 250 or 300 g/l tends to be unstable.
  • compositions do not contain greater than 400 grams per litre of bipyridylium ion.
  • an aqueous agrochemical composition comprising paraquat or diquat or a mixture thereof; and an adjuvant selected from a salt of quinuclidine, a salt of N- (aminopropyl)morphiline, 1-(2-hydroxethyl-2-imidazolidinone) or a salt of aminoethylpiperazine.
  • an aqueous agrochemical composition comprising paraquat or diquat and a salt of quinuclidine, a salt of N-(aminopropyl) morphiline, 1-(2-hydroxethyl-2- imidazolidinone) or a salt of aminoethylpiperazine, wherein the concentration of the paraquat or diquat is greater than 100 g/l.
  • the pH of the paraquat or diquat composition of the invention will be from 3.0 to 8.0 and preferably from 4.0 to 8.0.
  • the pH of the amine is adjusted with acid approximately to that of the paraquat or diquat composition and those nitrogen atoms of the amine which are sufficiently basic become protonated.
  • amines generally tend to represent a dermatological hazard, a much reduced problem is encountered with the partially neutralized amines used in the present invention.
  • the scope of the present invention is not limited to any particular bipyridyl composition, the invention is particularly suitable for use with an aqueous formulation of a bipyridylium herbicide such as those described in WO 02/076212 A1.
  • WO 02/076212 there are described the use of an alginate as a pH-triggered gelling agent in the manufacture of a herbicide composition
  • a herbicide composition comprising a salt of paraquat, a salt of diquat or a mixture thereof.
  • the composition further comprises an emetic and/or purgative such that a pH-triggered gel effect takes place at the acid pH of human gastric juice compositions. It is generally desirable to include one or more surfactants or adjuvants in such compositions to improve the bioperformance of the herbicide. A number of possible adjuvants are listed in WO 02/076212.
  • the composition also preferably contains a purgative such as magnesium sulphate.
  • WO 02/076212 recommends that when the composition of the invention contains a purgative, preferably magnesium sulphate, the concentration of magnesium sulphate is preferably from 10 to 400 grams per litre of the composition, and more preferably from 10 to 100 grams per litre.
  • magnesium sulphate for example up to 400 grams per litre, may be used and may continue to provide increased purgative effect but such high levels of magnesium sulphate may have an adverse effect on formulation stability.
  • formulation stability may also be compromised at concentrations below 400 g/l, for example around 100 g/l.
  • physical incompatibility in relation to adjuvants used in bipyridyl compositions indicates either gross separation of one or more components of the composition which may or may not be accompanied by a significant change in formulation rheology or bulk homogeneity. It is not necessarily essential that the composition is fully homogeneous in a strict physical sense provided that the composition is substantially homogeneous in the bulk.
  • a slight separation of a second phase may be acceptable provided that the separated phase remains fully dispersed in the bulk. If however any separated phase is not fully dispersed in the bulk, but for example rises to the surface of the composition, the composition may not show bulk homogeneity and a sample taken from one portion of the bulk may have a different composition from a sample taken from a different portion of the bulk. This is obviously undesirable for a number of reasons.
  • the term physical compatibility indicates the reverse of physical incompatibility as defined above.
  • compositions of WO 02/076212 containing about 120 g/l paraquat ion and about 80 g/l diquat ion in the presence of an alginate and about 120 g/l of magnesium sulphate heptahydrate may show physical incompatibility, when it is attempted to incorporate many of the adjuvants listed therein.
  • physical separation was observed when tallow amine ethoxylate was incorporated at levels above about 10 g/l.
  • Two phases were formed when it was attempted to incorporate a sodium salt of dodecyl benzene sulphonate at levels above about 10 g/l.
  • an aqueous agrochemical composition comprising paraquat or diquat and a salt of quinuclidine, a salt of N-(aminopropyl) morphiline, 1-(2-hydroxethyl-2- imidazolidinone) or a salt of aminoethylpiperazine wherein the concentration of the paraquat or diquat is greater than 100 g/l and which further contains from 10 to 400 grams per litre, for example from 10 to 100 grams per litre of an electrolyte purgative such as magnesium sulphate.
  • an aqueous agrochemical composition comprising paraquat or diquat and a salt of quinuclidine, a salt of N-(aminopropyl) morphiline, 1-(2-hydroxethyl-2- imidazolidinone) or a salt of aminoethylpiperazine wherein the concentration of the paraquat or diquat is greater than 100 g/l and which further comprises an alginate which is a pH-triggered gelling agent, such that a pH-triggered gel effect takes place at the acid pH of human gastric juice, together with from 10 to 400 grams per litre, for example from 10 to 100 grams per litre, of an electrolyte purgative, such as magnesium sulphate.
  • an electrolyte purgative such as magnesium sulphate.
  • the amines or amides of the present invention when used as sole adjuvant may provide effective bioperformance enhancement.
  • the second adjuvant is preferably a surfactant.
  • the surfactant There is no particular limitation on the surfactant that may be used and numerous examples will occur to those skilled in the art. We have found that anionic, cationic, nonionic, amphoteric or Zwitterionic surfactants may be effective.
  • the second adjuvant also exhibits acceptable compatibility, for example with compositions such as those described in WO 02/076212, although the second adjuvant may well be present at a lower concentration than that of the amine or amide adjuvant of the present invention, so that this aspect may not be as crucial.
  • suitable second adjuvants there may be mentioned alkyl polyglycosides, betaines, alkylethoxy phosphates and salts thereof, alcohol ether carboxylic acids and salts thereof, alcohol ether sulphates and salts thereof.
  • second adjuvants that may exhibit physical incompatibility at higher concentrations but may still be acceptable if incorporated at relatively lower levels compared with the amine adjuvant
  • alcohol ethoxylates amine ethoxylates
  • amine oxides amine oxides
  • cationics such as quaternary ammonium salts.
  • suitable alkylpolyglycosides APG's
  • C 8- ⁇ 0 alkyl polyglycosides with a degree of polymerisation of 1.5-2.0 commercially available examples include AQNIQUE 8107-U
  • amine ethoxylates there may be mentioned for example C 12 . 18 alkyl amine ethoxylates (5-50 moles).
  • examples include SYNPROLAM 35X15, ETHOMEEN C25 or T25.
  • examples of quaternary ammonium salts and ethoxylated quaternary ammonium salts include C 8 - ⁇ alkyltrialkyl ammonium halides (commercially available examples include ARQUAD 16-50).
  • examples of amine oxides include C ⁇ 2 - 18 saturated or unsaturated alkyl- dimethyl amine oxides (commercially available examples include AROMOX MCD-W).
  • betaines include for example alkyldimethyl betaines and alkylamidopropyl betaines, where alkyl chain length can be C 12-18 (commercially available examples include TEGOBETAINE F50).
  • alkylethoxyphosphates include for example C 4-18 alkylethoxy (2-10 moles) mono-,di- or sesqui- phosphate esters (as acid, inorganic or organic salts).
  • Commercially available examples include CRODAFOS T5A, N10A and GERONOL CF/AR.
  • alcohol ether carboxylates include for example those of C 8 . ⁇ 8 alcohol ethoxylate (2-15 moles) carboxylates (as acid, inorganic or organic salts).
  • Commercially available examples include EMPICOL CBF, CBJ, and CED-5.
  • alcohol ether sulphates include for example C 8- 8 alcohol ethoxylate (2-10 moles) sulphates (as acid, inorganic or organic salts).
  • Commercially available examples include EMPICOL EAC70, EGC70, and ESC70.
  • the amines or amides of the present invention may form a salt with an anionic surfactant or a surfactant having an acidic form. If desired, such a salt may be pre-formed by the reaction of the amines of the present invention with the anionic surfactant, for example in aqueous solution, but there is no particular need for such pre-reaction.
  • the ratio by weight of the amines or amides of the present invention to the second adjuvant or co-adjuvant may vary within wide limits, for example from 50:1 to 1 :50, and in particular from 10:1 to 1 :10 by weight.
  • the ratio by weight of the amines or amides of the present invention to the agrochemical active ingredient is preferably from 1 :20 to 10:1 , for example from 1 :10 to 1 :2.
  • the ratio by weight of the total adjuvant is preferably from 1 : 10 to 10: 1 , for example from 1 :5 to 10: 1.
  • the composition may contain further additives conventional in the art. The invention is illustrated by the following Examples in which all parts and percentages are by weight unless otherwise stated.
  • EXAMPLE 1 The bioperformance enhancement of paraquat in the presence of amines or amides of the present invention was evaluated. The amines or amides were tested and the results are presented in Table 1.
  • aminoethylpiperazine the formulation contained 0.625% by weight of the amine (based on the parent amine).
  • Examples 2 and 3 A composition of WO 02/076212 containing 200 g/l paraquat and 72 g/l of total adjuvants together with an alginate gelling agent was evaluated for biological activity using the following method: Field Trials were conducted at 8 locations where the target plants were a range of drilled broad leaved & grass weeds. The 200 g/l paraquat compositions were applied as a foliar spray at application rates of 75, 150 & 300g/ha paraquat ion, and at an application volume of 2001/ha at a weed growth stage when the grasses were tillering & the broadleaved weeds were branching. (Note.
  • 0% weed control represents no herbicidal effect and 100% weed control represents complete kill
  • the adjuvants used were selected from those exemplified in WO 02/076212.
  • 28 g/l of the 72 g/l of total adjuvant used in Comparison 1 was replaced with AEP.
  • 37 g/l of the total adjuvant used in Comparison 1 was replaced with AEP.
  • the results, expressed as % weed control, were assessed 7 days after application and are a mean of all rates applied and the mean of all species tested. The mean of all replicates & a mean of all field trials were as follows:

Abstract

La présente invention concerne des compositions agrochimiques et, plus particulièrement, des compositions agrochimiques aqueuses contenant un ingrédient actif agrochimique soluble dans l'eau et un adjuvant ; de préférence des amines cycliques ou des amides cycliques comportant au moins une amine tertiaire ou de l'azote tertiaire. Les amines ou amides de la présente invention sont de préférence une amine ou un amide sélectionné dans le groupe comprenant de la quinuclidine ou un sel de la quinuclidine, de la N-(aminopropyle)morphiline ou un sel de la N-(aminopropyle)morphiline, de la 1-(2-hydroxéthyl-3-imidazolidinone) et de l'aminoéthylpipérazine ou un sel d'aminoéthylpipérazine.
PCT/GB2004/005002 2003-12-09 2004-11-26 Compositions agrochimiques WO2005055722A1 (fr)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US10/578,211 US20070082818A1 (en) 2003-12-09 2004-11-26 Agrochemical compositions
CA002546780A CA2546780A1 (fr) 2003-12-09 2004-11-26 Compositions agrochimiques
JP2006543604A JP2007513932A (ja) 2003-12-09 2004-11-26 農芸化学組成物
EA200601083A EA011571B1 (ru) 2003-12-09 2004-11-26 Агрохимические композиции
BRPI0417405-4A BRPI0417405A (pt) 2003-12-09 2004-11-26 composições agroquìmicas
EP04769042A EP1694124A1 (fr) 2003-12-09 2004-11-26 Compositions agrochimiques
UAA200607534A UA83706C2 (en) 2003-12-09 2004-11-26 Agrochemical composition
AU2004296585A AU2004296585B2 (en) 2003-12-09 2004-11-26 Agrochemical compositions
NZ547047A NZ547047A (en) 2003-12-09 2004-11-26 Agrochemical compositions
AP2006003673A AP2231A (en) 2003-12-09 2004-11-26 Agrochemical compositions.
IL175739A IL175739A0 (en) 2003-12-09 2006-05-18 Agrochemical compositions
NO20062295A NO20062295L (no) 2003-12-09 2006-05-22 Agrokjemiske sammensetninger
TNP2006000172A TNSN06172A1 (en) 2003-12-09 2006-06-05 Agrochemical compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0328529.3 2003-12-09
GBGB0328529.3A GB0328529D0 (en) 2003-12-09 2003-12-09 Agrochemical composition

Publications (1)

Publication Number Publication Date
WO2005055722A1 true WO2005055722A1 (fr) 2005-06-23

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2004/005002 WO2005055722A1 (fr) 2003-12-09 2004-11-26 Compositions agrochimiques

Country Status (28)

Country Link
US (1) US20070082818A1 (fr)
EP (1) EP1694124A1 (fr)
JP (1) JP2007513932A (fr)
CN (1) CN100471393C (fr)
AP (1) AP2231A (fr)
AR (1) AR046761A1 (fr)
AU (1) AU2004296585B2 (fr)
BR (1) BRPI0417405A (fr)
CA (1) CA2546780A1 (fr)
CR (1) CR8425A (fr)
EA (1) EA011571B1 (fr)
EC (1) ECSP066624A (fr)
GB (1) GB0328529D0 (fr)
GE (1) GEP20084563B (fr)
GT (1) GT200400260A (fr)
HN (1) HN2004000523A (fr)
IL (1) IL175739A0 (fr)
MA (1) MA28283A1 (fr)
NO (1) NO20062295L (fr)
NZ (1) NZ547047A (fr)
PA (1) PA8619801A1 (fr)
PE (1) PE20050703A1 (fr)
TN (1) TNSN06172A1 (fr)
TW (1) TWI318865B (fr)
UA (1) UA83706C2 (fr)
UY (1) UY28663A1 (fr)
WO (1) WO2005055722A1 (fr)
ZA (1) ZA200604722B (fr)

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WO2013079549A1 (fr) * 2011-12-02 2013-06-06 Rhodia Operations Composition agrochimique

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070082819A1 (en) * 2003-12-09 2007-04-12 Perry Richard B Agrochemical compositions
EP2460404A1 (fr) * 2010-12-01 2012-06-06 Basf Se Compositions contenant des sels de polyamine identiques de pesticides anioniques mélangés
GB2496327B (en) * 2012-12-24 2016-04-20 Rotam Agrochem Int Co Ltd Method of improving plant growth with clomazone
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AU2004296585B2 (en) 2010-09-23
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ZA200604722B (en) 2007-03-28
EA200601083A1 (ru) 2006-12-29
BRPI0417405A (pt) 2007-04-10
AP2006003673A0 (en) 2006-08-31
UY28663A1 (es) 2005-07-29
EP1694124A1 (fr) 2006-08-30
EA011571B1 (ru) 2009-04-28
UA83706C2 (en) 2008-08-11
PE20050703A1 (es) 2005-09-05
GT200400260A (es) 2005-08-18
CR8425A (es) 2006-10-04
HN2004000523A (es) 2007-12-14
PA8619801A1 (es) 2006-03-24
MA28283A1 (fr) 2006-11-01
CN100471393C (zh) 2009-03-25
AR046761A1 (es) 2005-12-21
AU2004296585A1 (en) 2005-06-23
TW200526124A (en) 2005-08-16
NO20062295L (no) 2006-08-31
IL175739A0 (en) 2006-09-05
NZ547047A (en) 2009-09-25
TWI318865B (en) 2010-01-01
GEP20084563B (en) 2008-12-10
CN1889839A (zh) 2007-01-03
AP2231A (en) 2011-05-04
US20070082818A1 (en) 2007-04-12
CA2546780A1 (fr) 2005-06-23
GB0328529D0 (en) 2004-01-14

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